US9750812B2 - Lipid based pharmaceutical preparations for oral and topical application; their compositions, methods, and uses thereof - Google Patents
Lipid based pharmaceutical preparations for oral and topical application; their compositions, methods, and uses thereof Download PDFInfo
- Publication number
- US9750812B2 US9750812B2 US13/120,127 US200913120127A US9750812B2 US 9750812 B2 US9750812 B2 US 9750812B2 US 200913120127 A US200913120127 A US 200913120127A US 9750812 B2 US9750812 B2 US 9750812B2
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- United States
- Prior art keywords
- composition
- finasteride
- lipid
- acid
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 206
- 150000002632 lipids Chemical class 0.000 title claims abstract description 150
- 238000000034 method Methods 0.000 title abstract description 37
- 230000000699 topical effect Effects 0.000 title abstract description 11
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 claims abstract description 112
- 229960004039 finasteride Drugs 0.000 claims abstract description 110
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229960003632 minoxidil Drugs 0.000 claims abstract description 44
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 claims abstract description 8
- 229960001967 tacrolimus Drugs 0.000 claims abstract description 8
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 claims abstract description 8
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 claims abstract description 6
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims abstract description 6
- 229960003942 amphotericin b Drugs 0.000 claims abstract description 6
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 89
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 84
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 84
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- 231100000252 nontoxic Toxicity 0.000 claims description 26
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- 150000003904 phospholipids Chemical class 0.000 claims description 24
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- 150000004665 fatty acids Chemical class 0.000 claims description 12
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 12
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- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims description 6
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- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 claims description 4
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 4
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- BIABMEZBCHDPBV-MPQUPPDSSA-N 1,2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol) Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCC BIABMEZBCHDPBV-MPQUPPDSSA-N 0.000 claims description 4
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- RJECHNNFRHZQKU-UHFFFAOYSA-N Oelsaeurecholesterylester Chemical class C12CCC3(C)C(C(C)CCCC(C)C)CCC3C2CC=C2C1(C)CCC(OC(=O)CCCCCCCC=CCCCCCCCC)C2 RJECHNNFRHZQKU-UHFFFAOYSA-N 0.000 claims description 3
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- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- acids include, but are not limited to, hydrochloric, hydrobromic, sulfuric, nitric, perchloric, fumaric, maleic, phosphoric, glycolic, lactic, salicylic, succinic, toluene-p-sulfonic, tartaric, acetic, citric, methanesulfonic, ethanesulfonic, formic, benzoic, malonic, sulfonic, naphthalene-2-sulfonic, benzenesulfonic acid, and the like.
- Other acids such as oxalic, while not in themselves pharmaceutically acceptable, may be employed in the preparation of salts useful as intermediates in obtaining the compounds of the invention and their pharmaceutically acceptable acid addition salts.
- active agent-lipid composition for example, finasteride-lipid composition contain cholesterol or cholesterol derivatives.
- cholesterol derivatives that find use in the present invention include but are not limited to cholesteryl sulfate, cholesteryl hemisuccinate, cholesteryl succinate, cholesteryl oleate, cholesteryl linoleate, cholesteryl eicosapentenoate, cholesteryl linolenate, cholesteryl arachidonate, cholesteryl palmitate, cholesteryl stearate, cholesteryl myristate, polyethylene glycol derivatives of cholesterol (cholesterol-PEG), water soluble cholesterol (for example, cholesterol methyl- ⁇ -cyclodextrin), coprostanol, cholestanol, or cholestane, cholic acid, cortisol, corticosterone or hydrocortisone and 7-dehydrocholesterol.
- cholesterol derivatives that find use in the present invention include but are not limited to
- compositions that find use in the present invention include but are not limited to solutions, suspensions, emulsions, ointments; suppositories, gels can be suitable pharmaceutical preparations.
- active compound-lipid composition for example, finasteride-lipid composition
- active compound-lipid composition is provided in the form of solutions, gels, oils, and emulsions, such as are known by the addition of suitable water-soluble or water-insoluble excipients, for example polyethylene glycols, certain fats, and esters, compounds having a higher content of polyunsaturated fatty acids and derivatives thereof.
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- Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Dispersion Chemistry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cosmetics (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/120,127 US9750812B2 (en) | 2008-09-27 | 2009-09-25 | Lipid based pharmaceutical preparations for oral and topical application; their compositions, methods, and uses thereof |
Applications Claiming Priority (3)
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|---|---|---|---|
| US10071408P | 2008-09-27 | 2008-09-27 | |
| PCT/US2009/058463 WO2010036947A2 (en) | 2008-09-27 | 2009-09-25 | Lipid based pharmaceutical preparations for oral and topical application; their compositions, methods, and uses thereof |
| US13/120,127 US9750812B2 (en) | 2008-09-27 | 2009-09-25 | Lipid based pharmaceutical preparations for oral and topical application; their compositions, methods, and uses thereof |
Publications (2)
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| US20110212167A1 US20110212167A1 (en) | 2011-09-01 |
| US9750812B2 true US9750812B2 (en) | 2017-09-05 |
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| US13/120,127 Active 2033-06-27 US9750812B2 (en) | 2008-09-27 | 2009-09-25 | Lipid based pharmaceutical preparations for oral and topical application; their compositions, methods, and uses thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US9750812B2 (enExample) |
| EP (1) | EP2344198B1 (enExample) |
| JP (3) | JP2012504135A (enExample) |
| CA (1) | CA2737025C (enExample) |
| CY (1) | CY1123579T1 (enExample) |
| DK (1) | DK2344198T3 (enExample) |
| ES (1) | ES2834006T3 (enExample) |
| HR (1) | HRP20201860T1 (enExample) |
| HU (1) | HUE052571T2 (enExample) |
| LT (1) | LT2344198T (enExample) |
| MX (1) | MX2011003207A (enExample) |
| PL (1) | PL2344198T3 (enExample) |
| PT (1) | PT2344198T (enExample) |
| SI (1) | SI2344198T1 (enExample) |
| WO (1) | WO2010036947A2 (enExample) |
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| US20220339282A1 (en) * | 2018-11-29 | 2022-10-27 | Glaxosmithkline Biologicals Sa | Methods for manufacturing an adjuvant |
| US11850300B2 (en) | 2022-03-17 | 2023-12-26 | Rally Guide | Topical lotion composition, methods of use, and methods of preparation |
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| EP2344198A4 (en) | 2013-01-09 |
| PL2344198T3 (pl) | 2021-05-31 |
| EP2344198B1 (en) | 2020-11-04 |
| ES2834006T3 (es) | 2021-06-16 |
| LT2344198T (lt) | 2021-02-25 |
| CA2737025A1 (en) | 2010-04-01 |
| WO2010036947A3 (en) | 2010-06-10 |
| JP2014221784A (ja) | 2014-11-27 |
| WO2010036947A2 (en) | 2010-04-01 |
| MX2011003207A (es) | 2011-11-04 |
| HUE052571T2 (hu) | 2021-05-28 |
| SI2344198T1 (sl) | 2021-01-29 |
| PT2344198T (pt) | 2020-12-04 |
| EP2344198A2 (en) | 2011-07-20 |
| JP2012504135A (ja) | 2012-02-16 |
| JP2017048188A (ja) | 2017-03-09 |
| JP6196943B2 (ja) | 2017-09-13 |
| US20110212167A1 (en) | 2011-09-01 |
| CA2737025C (en) | 2012-09-04 |
| HRP20201860T1 (hr) | 2021-04-16 |
| CY1123579T1 (el) | 2022-03-24 |
| DK2344198T3 (da) | 2020-11-30 |
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